"Four different pieces" – Shark Tank star Kevin O’Leary reveals how many times he swaps watches in a single day

Shark Tank investor Kevin O'Leary shared a video on his Instagram page on February 8, 2025, explaining his daily watch-swapping habit. In the video, he stated that he changes his watches four times a day.

Elaborating on his process, he said that he wanted "real diversity" when it came to his watches, noting that he was "at the point" where he wore four different watches in one day.

"Think about watch collecting, you want to go into your vault and say, what am I going to wear today? Now I’m at the point, I’m wearing up to four different pieces a day. So, I want real diversity. I know that sounds crazy," the investor said.

O'Leary explained that he wears one watch in the morning before switching to the second one at lunch. He noted that he then changes the watch in the late afternoon before a bike ride and ends his day with a statement piece.

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Shark Tank star Kevin O’Leary's take on watch collection

Shark Tank investor Kevin O’Leary is a passionate watch collector and often shares insights into his collection and preferences on social media. His decision to wear multiple watches daily is driven by diversity, function, and style. Instead of sticking to a single timepiece, O’Leary believes in selecting a watch that aligns with his activities and attire.

O’Leary’s collection is not just about aesthetics but also financial value. He has often discussed how well-curated watch collections can serve as strong investments. Some timepieces appreciate over time, making them valuable assets beyond just being accessories.

His love for watches extends beyond just wearing them, as O’Leary frequently shares details about different models, movements, and craftsmanship. He has highlighted pieces like the Louis Erard Excellence Regulateur Lapis Lazuli, known for its Swiss craftsmanship and unique stone dial.

He noted the challenges in cutting and shaping Lapis Lazuli, stating that the process is difficult due to the stone’s tendency to break. The watch features three displays for hours, minutes, and seconds, with a distinct design inspired by precision timekeeping.

Shark Tank's Kevin O’Leary is also known for his insights on accessible luxury watches. He shared a video discussing entry-level timepieces for new collectors on January 11, 2025. The investor praised brands like Grand Seiko and Tudor for their ability to provide high-quality watches under $10,000. He stated that he liked the brands that cared about the new collector.

"Grand Seiko has production capacity, so it's not only important enough to make an entry-level, but they also actually have inventory you can buy. Tudor the same, because it's great to bring out a watch for $5,000 and make four, like Seuss,” he explained.

Beyond collecting, Shark Tank investor O’Leary emphasizes the role of watches in professional settings. He attended Cityscape, a real estate conference in Riyadh, Saudi Arabia, on January 4, 2025, where he discussed the importance of selecting the right watch for networking.

"You've got to bring your A-game, even with your watches," he said.

During the event, the Shark Tank star showcased models like the Meteorite Daytona and the Moser Derby. He explained how the watches symbolize sophistication and success. He noted that the Rolex Meteorite Daytona features a dial made from extraterrestrial material, making it a rare and unique timepiece.

"It's gold, it's unique, and it connects you to the artistry of Rolex and space," he said in a past video.

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